Diisopropylethylamine → HCID 39733378, compound

HRID 1848374Notes

Reaction equation

HRID 1848374 reaction equation
[CH2:1]([N:3]1[C:7](=[O:8])[C:6](=[O:9])[CH:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4]1)[CH3:2].[CH3:15]CN(C(C)C)C(C)C>C(#N)C.CO>[CH2:1]([N:3]1[C:7](=[O:8])[C:6]([O:9][CH3:15])=[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 219264ethyl 1-ethyl-4,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 39733378HCID 39733378, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1-ethyl-4,5-dioxopyrrolidine-3-carboxylate (200 mg, 1.0 mmol) and DIPEA (0.18 mL, 1.0 mmol) in ACN (1.8 mL) and MeOH (0.2 mL) was added TMS-CH2N2 (2.0 M in Et2O; 0.5 mL, 1.0 mmol). The reaction mixture was stirred at rt for 3.5 h, then evaporated in vacuo. The product was purified by silica gel chromatography (40 g silica gel; linear gradient of 0-50% MeOH:EtOAc (10:1) in hexanes over 15 min) to obtain Intermediate 9A (203 mg, 95% yield). HPLC/MS (Method D) RT=0.73 min, [M+H]+ 214.2.

Workup

  1. customevaporated in vacuo
  2. customThe product was purified by silica gel chromatography (40 g silica gel; linear gradient of 0-50% MeOH:EtOAc (10:1) in hexanes over 15 min)

Sources & evidence

ORD record
ord-576d958ddcb54b538662b05cb18ba3bf
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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